Structural characterization of a new amino acid derivatives, Maillard Reaction product of red ginseng and potential protective activity against cisplatin-evoked intestinal injury

Abstract

Based on the Maillard reaction principle of red ginseng (Panax ginseng C.A. Meyer), this study innovatively synthesized a new amino acid derivative by combining arginine with lactose through simulated synthesis, and was separated and purified through repeated silica gel and polyacrylamide gel (Bio-gel P-II) column chromatography. The purity of the product was determined to be 99.86% and its molecular weight was determined to be 497.3612 (negative ion mode) by electrospray ionisation mass spectrometry (ESI-MS). The chemical structure was identified to be 1-(arginine-Nαgroup)-1-deoxy-4-O-(α-D-galactopyranosyl)-D-fructose, named Argininyl-fructosyl-galactose (AFGA, C18H34N4O12). Subsequently, by establishing cisplatin-induced intestinal injury in vivo and IEC-6 cell model, the results showed that pretreatment with AFGA significantly ameliorated cisplatin induced oxidative stress by reducing levels of reactive oxygen species (ROS) in IEC-6 cells (p<0.05, p<0.01), and could effectively reduce the secretion of pro-inflammatory factors in serum and the expression level of NF-κB protein in intestinal tissues (p<0.01). Meantime, AFGA also inhibited the expression of p-PI3K/p-Akt, caspase 3, 9, cytochrome C and Bax protein intestinal tissue in mice (p<0.01), and promoted the expression of Bcl-2 protein (p<0.01). Importantly, the molecular docking results of AFGA also suggested a better binding ability with the above-mentioned related target proteins, and further revealed AFGA as a potential multifunctional therapeutic agent with clear protective effect against cisplatin-induced intestinal injury.